CN106947395B - Preparation method of light-colored polymerized rosin - Google Patents
Preparation method of light-colored polymerized rosin Download PDFInfo
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- CN106947395B CN106947395B CN201710115643.4A CN201710115643A CN106947395B CN 106947395 B CN106947395 B CN 106947395B CN 201710115643 A CN201710115643 A CN 201710115643A CN 106947395 B CN106947395 B CN 106947395B
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- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 63
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 63
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 23
- 239000008158 vegetable oil Substances 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 241000779819 Syncarpia glomulifera Species 0.000 claims abstract description 17
- 239000001739 pinus spp. Substances 0.000 claims abstract description 17
- 229940036248 turpentine Drugs 0.000 claims abstract description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical group C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 5
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 244000043261 Hevea brasiliensis Species 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- 229920003052 natural elastomer Polymers 0.000 claims description 4
- 229920001194 natural rubber Polymers 0.000 claims description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 4
- 235000019483 Peanut oil Nutrition 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 3
- 235000021388 linseed oil Nutrition 0.000 claims description 3
- 239000000944 linseed oil Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000000312 peanut oil Substances 0.000 claims description 3
- 239000003549 soybean oil Substances 0.000 claims description 3
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- 229910045601 alloy Inorganic materials 0.000 claims description 2
- 239000000956 alloy Substances 0.000 claims description 2
- 239000001293 FEMA 3089 Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 4
- 238000004040 coloring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 229910001252 Pd alloy Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of light-colored polymerized rosin, which comprises the following steps: adding polymerized rosin and turpentine into a reaction kettle, adding a catalyst and vegetable oil, introducing hydrogen, heating to 80-300 ℃ under the pressure of 5-35 MPa, carrying out hydrogenation reaction for 1-6 hours, and removing the solvent under reduced pressure to obtain the light-colored polymerized rosin. Wherein the catalyst is palladium carbon, palladium aluminum oxide, nickel or vegetable oil. Wherein the mass ratio of the polymerized rosin, the turpentine oil, the vegetable oil and the catalyst is 1: 1-5: 0.05-0.3: 0.01-0.1. The product of the invention has light color and good stability, and can be applied to industries of high-grade adhesives, coatings, printing ink and the like.
Description
Technical Field
The invention belongs to the technical field of organic chemistry. In particular to a preparation method of light-colored polymerized rosin.
Background
Polymerized rosin is one of rosin modified varieties and is an important chemical raw material. The polymerized rosin has the advantages of high softening point, light color, difficult crystallization, excellent oxygen resistance, good miscibility with a film forming agent, higher viscosity in an organic solvent and the like, thereby being widely applied to the industries of coatings, paints, printing inks, papermaking and the like.
Polymerized rosin light-coloring technical research ([ D ] Libalin, 2004-Guangxi university: applied chemistry) rosin as a raw material improves the applicability of rosin polymerization process conditions, and particularly researches and develops the light-coloring technology. The paper considers the influence of the conditions of catalyst, solvent, reaction temperature and time, additive, settling separation, washing process and the like on the conversion rate of rosin polymerization reaction and technical indexes of product quality, discusses the influence of mixed catalyst, reaction temperature regulation and control, clarification separation temperature and the like on the color of the product, and determines proper process condition parameters. The method for improving the color of the polymerized rosin product is mainly concerned, and results show that 7 chemicals have a certain effect on improving the color of the product, the antioxidant A and the antioxidant G are effective light-color antioxidants, the addition amount of the antioxidant A and the antioxidant G is only 1-2 thousandth of the mass of the rosin, and the color improvement effect is very obvious. The quality technical indexes of polymerized rosin prepared by small tests reach that the softening point is 136-145 ℃, the color number of Gardner is 6-7 # (the color grade of rosin is super-grade-first grade), and the content of dimer is also increased to about 50-65% from 25-35% of the traditional sulfuric acid method; the acid value is high, the acid value can reach 140-150 mgKOH/g or even higher, the yield is 80-88%, the quality technical indexes such as hot water soluble substances, ethanol insoluble substances and the like are qualified through detection, and the product is superior to the quality requirements of national ministry of forestry standard ZBB 72998-89. The polymerized rosin light-coloring technology researched by the method has the advantages of complex process, more used reagents, high cost and no industrial production prospect.
With the continuous development of social economy, the quality requirement of the market on the polymerized rosin is continuously improved, and the color of the polymerized rosin is one of important requirements. The prior traditional preparation of light-colored polymerized rosin can not meet the application requirements, and the light-colored polymerized rosin is required to meet the market demand.
Disclosure of Invention
The invention aims to provide a preparation method of light-colored polymerized rosin, and the light-colored polymerized rosin prepared by the method has white color.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a preparation method of light-colored polymerized rosin comprises the following steps: adding polymerized rosin and turpentine into a reaction kettle, adding a catalyst and vegetable oil, introducing hydrogen after isolating oxygen, heating to 80-300 ℃ under the pressure of 5-35 MPa, reacting for 1-10 hours, and pressurizing to remove a solvent to obtain the light-colored polymerized rosin.
As a further improvement of the technical scheme, the catalyst is one of palladium carbon, palladium aluminum trioxide and alloy nickel.
As a further improvement of the technical scheme, the mass ratio of the polymerized rosin, the turpentine oil, the vegetable oil and the catalyst is 1: 1-5: 0.05-0.3: 0.01-0.1.
As a further improvement of the technical scheme, the mass ratio of the polymerized rosin, the turpentine oil, the vegetable oil and the catalyst is 1:3:0.1: 0.03.
As a further improvement of the technical scheme, the quality technical indexes of the light-color polymerized rosin reach that the heat stability is high, the polymerized rosin is stored for 3 days at the temperature of 200 ℃, and the color is not changed; the Gardner color number is less than No. 3; the compatibility with natural rubber and styrene butadiene rubber is good; the softening point is more than 120, and the acid value is 130-150.
As a further improvement of the technical proposal, the vegetable oil is selected from one or a mixture of more than two of peanut oil, soybean oil, linseed oil, castor oil and rapeseed oil.
Due to the adoption of the scheme, compared with the prior art, the invention has the following beneficial effects:
1. the invention can prepare the light-colored polymerized rosin by adopting a one-step method, and compared with the prior art, the invention has the advantages of simple process equipment, easy control of process parameters, less reagent consumption and 30 percent saving of cost compared with the prior art.
2. The color of the light-colored polymerized rosin prepared by the method is lighter than that produced by the prior art, and the color of the light-colored polymerized rosin is less than No. 3; the thermal stability is high, the color is unchanged after the product is stored for 3 days at the temperature of 200 ℃; the oxidation resistance is better; the compatibility with natural rubber and styrene butadiene rubber is good; the softening point is more than 120, and the acid value is 130-150.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention.
Example 1 (mass ratio of polymerized rosin, turpentine, vegetable oil and catalyst 1:1:0.05:0.01)
200 g of polymerized rosin, 200 g of turpentine, 10 g of vegetable oil (peanut oil) and 2 g of palladium-carbon are added into a 2L reaction bottle, stirred at room temperature, then replaced by nitrogen for 3 times, introduced with hydrogen at 5 MPa, and slowly heated to 80 ℃ for reaction for 1 hour. The solvent was completely removed by the reaction to obtain a pale-colored polymerized rosin.
Example 2 (mass ratio of polymerized rosin, turpentine, vegetable oil and catalyst 1:2:0.1:0.03)
200 g of polymerized rosin, 400 g of turpentine, 20 g of vegetable oil (soybean oil) and 6 g of palladium aluminum oxide are added into a 2L reaction bottle, stirred at room temperature, replaced by nitrogen for 3 times, introduced with hydrogen at 10 MPa, and slowly heated to 150 ℃ for reaction for 3 hours. The solvent was completely removed by the reaction to obtain a pale-colored polymerized rosin.
Example 3 (mass ratio of polymerized rosin, turpentine, vegetable oil and catalyst 1:3:0.15:0.05)
200 g of polymerized rosin, 600 g of turpentine, 30 g of vegetable oil (linseed oil) and 10 g of nickel alloy are added into a 2L reaction bottle, stirred at room temperature, then replaced by nitrogen for 3 times, introduced with hydrogen gas at 15 MPa, and slowly heated to 200 ℃ for reaction for 5 hours. The solvent was completely removed by the reaction to obtain a pale-colored polymerized rosin.
Example 4 (mass ratio of polymerized rosin, turpentine, vegetable oil and catalyst 1:4:0.2:0.07)
200 g of polymerized rosin, 800 g of turpentine, 40 g of vegetable oil (castor oil) and 14 g of palladium carbon are added into a 2L reaction bottle, stirred at room temperature, then replaced by nitrogen for 3 times, introduced with hydrogen at 20 MPa, and slowly heated to 250 ℃ for reaction for 8 hours. The solvent was completely removed by the reaction to obtain a pale-colored polymerized rosin.
Example 5 (mass ratio of polymerized rosin, turpentine, vegetable oil and catalyst 1:5:0.3:0.1)
200 g of polymerized rosin, 1000 g of turpentine, 60 g of vegetable oil (rapeseed oil) and 20 g of palladium aluminum trioxide are added into a 2L reaction bottle, stirred at room temperature, then replaced by nitrogen for 3 times, introduced with hydrogen at 30 MPa, and slowly heated to 300 ℃ for reaction for 10 hours. The solvent was completely removed by the reaction to obtain a pale-colored polymerized rosin.
Example 6 (mass ratio of polymerized rosin, turpentine, vegetable oil and catalyst 1:3:0.1:0.03)
200 g of polymerized rosin, 600 g of turpentine, 20 g of vegetable oil (rapeseed oil) and 6 g of palladium alloy nickel are added into a 2L reaction bottle, stirred at room temperature, then replaced by nitrogen for 3 times, introduced with hydrogen at 20 MPa, and slowly heated to 200 ℃ for reaction for 5 hours. The solvent was completely removed by the reaction to obtain a pale-colored polymerized rosin.
Further, the light-colored polymerized rosin prepared as described above was subjected to a quality test in parallel experimental design, and the results were as follows: the thermal stability is high, the color is unchanged after the product is stored for 3 days at the temperature of 200 ℃; the Gardner color number is less than No. 3; the compatibility with natural rubber and styrene butadiene rubber is good; the softening point is more than 120, and the acid value is 130-150.
Claims (4)
1. A preparation method of light-colored polymerized rosin is characterized by comprising the following steps: the method comprises the following steps: adding polymerized rosin and turpentine into a reaction kettle, adding a catalyst and vegetable oil, introducing hydrogen after isolating oxygen, heating to 80-300 ℃ under the pressure of 5-35 MPa, reacting for 1-10 hours, and pressurizing to remove a solvent to obtain light-colored polymerized rosin; the catalyst is one of palladium carbon, palladium aluminum oxide and alloy nickel; the mass ratio of the polymerized rosin to the turpentine to the vegetable oil to the catalyst is 1: 1-5: 0.05-0.3: 0.01-0.1.
2. The process for the preparation of light-colored polymerized rosin according to claim 1, wherein: the mass ratio of the polymerized rosin to the turpentine to the vegetable oil to the catalyst is 1:3:0.1: 0.03.
3. The process for the preparation of light-colored polymerized rosin according to claim 1, wherein: the light-colored polymerized rosin has the quality technical index that the heat stability is high and is 200oC, storing for 3 days under the condition of no change of color; the Gardner color number is less than No. 3; the compatibility with natural rubber and styrene butadiene rubber is good; the softening point is more than 120, and the acid value is 130-150.
4. The process for the preparation of light-colored polymerized rosin according to claim 1, wherein: the vegetable oil is one or more of peanut oil, soybean oil, linseed oil, castor oil and rapeseed oil.
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| CN201710115643.4A CN106947395B (en) | 2017-03-01 | 2017-03-01 | Preparation method of light-colored polymerized rosin |
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| CN201710115643.4A CN106947395B (en) | 2017-03-01 | 2017-03-01 | Preparation method of light-colored polymerized rosin |
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| CN106947395B true CN106947395B (en) | 2020-04-10 |
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Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107603486B (en) * | 2017-09-20 | 2020-02-21 | 广西鼎弘树脂有限公司 | Light-colored high-stability polymerized rosin resin and preparation method thereof |
| CN107699137A (en) * | 2017-11-01 | 2018-02-16 | 南宁市青秀区嘉利林化有限公司 | A kind of method that high-quality newtrex pentaerythritol ester is prepared using crude product as raw material |
| CN107573853A (en) * | 2017-11-01 | 2018-01-12 | 南宁市青秀区嘉利林化有限公司 | A kind of method that light newtrex is produced using newtrex crude product as raw material |
| CN107573852A (en) * | 2017-11-01 | 2018-01-12 | 南宁市青秀区嘉利林化有限公司 | A kind of newtrex light new technology |
| CN107652896A (en) * | 2017-11-01 | 2018-02-02 | 南宁市青秀区嘉利林化有限公司 | A kind of method that light hydrogenated rosin is prepared using rosin as raw material |
| CN107699136A (en) * | 2017-11-01 | 2018-02-16 | 南宁市青秀区嘉利林化有限公司 | A kind of new technology that light product is prepared using polymerized rosin glycerol ester crude product |
| CN108587471B (en) * | 2018-01-09 | 2019-11-01 | 广西鼎弘树脂有限公司 | A kind of an ultra shallow color high stability disproportionated rosin and preparation method thereof |
| CN108559403B (en) * | 2018-01-09 | 2019-11-05 | 广西鼎弘树脂有限公司 | A kind of an ultra shallow color high stability acrylic acid rosin and preparation method thereof |
| CN111393996B (en) * | 2020-04-21 | 2022-02-15 | 广东科茂林产化工股份有限公司 | Polymerized rosin mixed ester and preparation method and application thereof |
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| CN104119801B (en) * | 2014-07-30 | 2016-01-20 | 广西众昌树脂有限公司 | The preparation method of polymerized rosin glycerol ester |
| CN106010267A (en) * | 2016-05-26 | 2016-10-12 | 广西众昌树脂有限公司 | Method for producing hydrogenated rosin |
| CN106010268A (en) * | 2016-05-26 | 2016-10-12 | 广西众昌树脂有限公司 | Method for producing hydrogenated rosin glyceride |
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Denomination of invention: A preparation method for light colored polymerized rosin Effective date of registration: 20230925 Granted publication date: 20200410 Pledgee: Bank of China Limited Chongzuo Branch Pledgor: GUANGXI DINGHONG RESIN CO.,LTD. Registration number: Y2023980058786 |
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